America’s Civil War: John Mosby and George Custer Clash in the Shenandoah Valley

The peaceful stream and lush, rich soil of the fertile Shenandoah Valley in western Virginia had long been considered a paradise by its fortunate residents. Stretching Southwest from Harper’s Ferry in northern Virginia, nestled between the protective Allegheny Mountains on the west and the rolling Blue Ridge Mountains to the east, the Shenandoah was replete with prosperous farms, bountiful grain fields and fattened livestock.

Known fondly as ‘the Valley’ by its occupants, many of whom were peaceable Dunkers and Quakers who had migrated from Pennsylvania to share in the Valley’s prosperity. The first two years of the Civil War left the Shenandoah relatively untouched. With the exception of confederate Lt. Gen. Stonewall Jackson’s stirring 1862 Valley campaign, most of the fighting occurred to the east, on the other side of the Blue Ridge Mountains. Fighting in the Valley had been comparatively more civilized; Union generals forbade the wanton destruction of property, and Southern civilians could successfully demand payment in gold for damages done to fence rails and farmland.

That changed dramatically in 1864 when a pair of brash, bold fighters squared off in the Shenandoah–Northern Brig. Gen. George Armstrong Custer and Confederate Partisan Ranger John Singleton Mosby. After them, the Valley would never be the same.

Custer was born in New Rumley, Ohio, on December 5, 1839, to Emmanuel H. and Maria Ward Custer. Although his father was a farmer and blacksmith, soldiering had been in the family since Custer’s great-grandfather, a Hessian officer, served with Burgoyne at Saratoga. Custer yearned to be a soldier as well, and after an unimpressive stint at West Point during which he displayed a fondness for pranks, he graduated at the bottom of his class on June 24, 1861.

Custer arrived at the Civil War battle lines in time to participate in the first clash at Bull Run in July 1861, and over the next two years his audacity in action brought him increasing renown. But early 1864, he had achieved the rank of brigadier general–the youngest general in the Union Army–and been favorably noticed by his commander-in-chief, President Abraham Lincoln. At an official reception, Lincoln met Custer’s wife, Elizabeth, and exclaimed, ‘So this is the young woman whose husband goes into a charge with a whoop and a shout.’

Tall, thin and agile, Custer dominated those around him with his blue eyes, long golden hair and distinctive scarlet necktie. Although he hated to be bested by a foe and could be abrupt and impetuous in the heat of battle, his friends knew him to be personable and warm.

His opponent in the Valley was a gifted military leader in his own right, one whose perfection of guerrilla-style warfare would sorely test Custer. John Singleton Mosby was born December 6, 1833, in Edgemont, Va. An excellent student, Mosby joined the Virginia bar in 1855 after being dismissed from the University of Virginia for shooting and wounding a fellow student.

With the start of hostilities, Mosby enlisted in the cavalry and, like Custer, took part in the Bull Run campaign. After being attached to Maj. Gen. J.E.B. Stuart’s staff, Mosby organized independent ranger operations in Virginia in early 1863, beginning with a unit of nine men. Mosby adapted quickly to this irregular form of warfare. After a skirmish, Mosby’s men returned to their own homes rather than to camp, agreeing to meet again at a future date and place. Each man acquired his own horse, arms and uniforms, but was entitled to share in whatever public or personal property was captured. Mosby was soon the only organized military force in northern Virginia, and so firmly ruled the area that it became known as ‘Mosby’s Confederacy.’

Medium in height with sharp features, Mosby generally wore a full, light beard which accented his deep gray eyes, bronzed face and yellow-brown hair. Studious and quiet by nature, he was about to be pitted against a man who was impetuous and loud. Opposites would meet on the common ground of the Shenandoah Valley.

A combination of hardball politics and equally toughminded military strategy brought these two men together. Lincoln faced a tough reelection campaign in 1864. The American people were tired of the long war, and there were growing indications they might take out their frustrations on election day. Lincoln sorely needed a battlefield victory to enhance his fortunes at the polls.

So far, Northern troops had been stymied in the Southern-leaning Shenandoah Valley, where a Confederate force under Lt. Gen. Jubal Early pushed to the outskirts of Washington near the end of July 1864. No matter which commander Lincoln and his new General-in-Chief, Ulysses S. Grant, sent to the Shenandoah, Union troops seemed unable to check the Confederates.

Grant realized a victorious campaign in the Valley would eliminate a major military headache. The Valley posed a constant threat to Washington because its axis ran straight at the Northern capital. Southern troops, continuously replenished by the Valley’s abundant crops, could easily be shifted into the Valley from farther south through the Blue Ridge Mountains’ numerous gaps. In effect, the Valley formed a Confederate highway aimed at the Northern nerve center.

On the other hand, the Valley could not be similarly used by the North, for the Valley led away from the Confederate capital at Richmond. The farther a Northern army marched up the Valley, the farther it moved from its bases of supplies, and it would always be subject to a Confederate flank or rear attack through the gaps. Grant concluded that since the fertile Valley was useless for Northern operations while being invaluable to his adversary, he must eliminate the Valley as a factor for both sides.

This would not be easy, as Confederate armies were running short of supplies and could ill-afford to lose the Valley’s cattle, flour, corn, fruits, poultry and dairy products. Grant also recognized that a potent Northern force in the Shenandoah would open Confederate General Robert E. Lee’s left flank to attack and also threaten important Southern railroad lines. The man he needed to accomplish such daunting objectives had to be a skilled fighter, someone who could spur his men into action and put an end to the seesaw type of battles that epitomized Valley warfare. The man Grant turned to was Maj. Gen. Philip H. Sheridan, then commander of cavalry for the Army of the Potomac.

Sheridan was then only 33 years old, but he had become one of Grant’s favorite officers. Sheridan was an energetic leader who possessed the rare ability to gain others’ respect without apparent effort. His troops quickly rallied around him; an officer compared Sheridan to ‘an electric shock… The only commander I ever met whose personal appearance in the field was an immediate and positive stimulus to battle.’

Grant left no doubt as to how Sheridan was to proceed. He ordered Sheridan to ‘Put himself south of the enemy and follow him to the death.’ Grant wanted Sheridan to rely on cavalry rather than infantry, telling him, ‘Let your headquarers be in the saddle.’ Sheridan was to ‘eat out Virginia clear and clean as far as they [soldiers] go, so that crows flying over it for the balance of the season will have to carry their provender with them. ‘

Harsh orders, indeed, and quite different from the relatively more genteel times in the early part of the war. But war breeds destruction, and the Civil War in 1864 was a changed conflict. It had become a war of attrition, and civilians and their homes were now considered fair targets.

In early August, Sheridan moved south with 36,000 men toward the section of Virginia known as ‘Mosby’s Confederacy,’ prepared to lay waste to the green Valley that had caused so many problems for the North. Advancing with Sheridan was one of his close friends, the commander of the Michigan Brigade, Brig. Gen. ‘Autie’ Custer.

Mosby did not wait long to greet the invaders. In the early morning mist of August 13, while a large Federal wagon train rested near Berryville, Va., a group of men approached out of the fog and started to set up two small cannon. None of the Northern guards paid much attention, figuring they must be friendly troops. Suddenly, the cannon blasted Federal wagons, decapitating a mule with one of the first shells and setting fire to a number of wagons. Mules still hitched to burning wagons ran in terror, dragging behind them roaring infernos.

In an instant, gray-clad cavalry swooped in, yelling and shooting as they charged. It was over in a matter of minutes, with Mosby’s victorious men capturing over 200 prisoners, 700 horses and mules, 200 cattle, and 100 supply wagons. In this manner, was Mosby serving notice that Federal troops had best be on guard in his personal territory.

Grant quickly responded to this stinging defeat by ordering Sheridan to send troops ‘through Loudoun County, to destroy and carry off the crops, animals, Negroes, and all men under fifty years of age capable of bearing arms. In this way, you will get many of Mosby’s men.’ He also ordered Sheridan to hunt down the families of Mosby’s men. ‘I think they should be taken and kept at Fort McHenry, or some other secure place, as hostages for the good conduct of Mosby’s men.’ Grant then ominously added ‘When any of Mosby’s men are caught, hang them without trial.’

Three days later, Grant’s orders were carried out when seven prisoners, thought to be Mosby’s Rangers, were executed . Although Mosby denied they were his men, he was already making plans to retaliate.

Sheridan had been in the Shenandoah for less than two weeks, and already the Valley was witnessing a more vulgar form of warfare than it had ever seen.

Mosby heard reports that Custer, in particular, was pursuing his orders with a special vengeance, he blamed Custer personally for the seven executions. Mosby’s men began calling Custer ‘Attila the Hun,’ and bitter feelings between Custer’s men and Mosby’s Confederate outfit quickly rose to a high pitch. In one action on August 18, Custer learned that a light at a local farmhouse had served as a signal for guerrillas; so Custer ordered it and all of the surrounding homes destroyed. As his men were setting fire to the elegant residences, a group of Mosby’s men led by J. G. L. William Chapman charged from an overlooking ridge, splashed through the Shenandoah River, and smacked into Custer’s outfit. Chapman exhorted his men to ‘Wipe them from the face of the earth! No quarter! No quarter! Take no prisoners!’

Custer’s squad was taken totally by surprise and fled in panic. A local woman watched as the Northern troops ‘hid behind the burning ruins, they crouched in the corners of fences, they begged for life, but their day of grace was past.’ One unfortunate young Northern soldier was taken prisoner and Chapman’s men demanded he be executed for what his comrades had done. The young prisoner impressed his captors with the courage with which he faced death. One Ranger, John Scott, wrote, ‘It was a solemn spectacle to see this brave young soldier kneel in the solitude of the mountain and pour forth a fervent prayer to the Great Father to pardon his sins…. The young man then rose slowly to his feet and tearing open his shirt, with unquailing eye received the fatal shot.’

Mosby’s own report of the incident to Lee’s headquarters mentioned that his men were so enraged at seeing Valley homes go up in smoke that ‘no quarter was shown, and about 25 of them [Custer’s men] were shot to death for their villainy. About 30 horses were brought off, but no prisoners.’ Horses were taken, but prisoners were shown no mercy. Warfare in the beautiful Shenandoah was begetting its own form of ugliness. As a chaplain in the 1st Rhode Island Cavalry bluntly uttered, ‘The time had fully come to peel this land.’

Mosby’s increased harrassment of Northern units brought even harsher Union devastation on Shenandoah farms. A vicious cycle was thus formed in the Valley–Sheridan’s men destroyed homes and farms because Mosby’s guerrillas hampered communications and ambushed isolated Northern units, while Mosby’s forces attacked with increasing ferocity because Sheridan’s men devastated the Shenandoah.

Custer’s infamy in the Valley increased when one of his cavalry charges proved to be decisive at the battle of Opequon Creek, resulting in the capture of 700 Confederates. By now Custer was so hated in the Shenandoah that Sheridan warned him against getting captured. ‘If the Rebs should ever lay you by the heels, they’ll string you up directly.’

Custer had to be constantly vigilant, for Mosby’s Rangers seemed to materialize everywhere. They were lightning-fast riders who used two revolvers rather than the unwieldy saber. The North had so much trouble getting supplies and messages to the front that one colonel estimated 500 cavalry would be needed to adequately protect a supply train. Northern cavalrymen so feared Mosby’s Rangers that some said they would rather charge into battle than patrol Valley roads.

The deeper Sheridan moved up the Valley, the more frequent and savage became guerrilla actions. Captain George Sanford of the 1st U.S. Cavalry said everyone was careful because ‘No party of less than 50 men was safe a mile from camp. The loss in men, animals and supplies was enormous. ‘

One of Sheridan’s aides was found in a field with his throat slit. In retaliation Sheridan ordered every house, barn, and outbuilding in a five-mile radius burned. Rations were so low at times that soldiers’ morale decreased. One group of 60 stunned Northern bathers was even captured nude, in the South Branch River while swimming.

Northern troops roundly condemned guerrilla actions as being cowardly and considered Mosby’s men ‘of all created beings most despicable.’ Famous poet Walt Whitman luridly wrote that Mosby’s men ‘would run a knife through the wounded, the aged, the children, without compunction.’

Without moral compunctions themselves, Sheridan’s men went about destroying the Valley. A newspaper correspondent who accompanied them wrote, ‘The atmosphere, from horizon to horizon, has been black with the smoke of a hundred conflagrations, and at night a gleam brighter and more lurid than sunset has shot from every verge…. The completeness of the devastation is awful. Hundreds of nearly starving people are going north…. not half the inhabitants of the Valley can subsist on it in its present condition.’ Confederate soldier Henry Douglas compared what he saw to a holocaust and tried ‘to restrain my bitterness (but) it is an insult to civilization and to God to pretend that the Laws of War justify such warfare.’

Invariably, warfare fought in such a brutal manner will lead to horrific atrocities. That is what happened on September 22, near the town of Front Royal, midway up the Valley. A Northern ambulance train was attacked by a group of Rangers led by Captain Sam Chapman, William’s brother. Chapman’s force quickly realized they were outnumbered, and in an attempt to break out, rode directly at Northern troops.

After the skirmish, the mangled body of Lieutenant Charles McMaster was found in the road, riddled with bullets and trampled by horses. Northern troops swore McMaster was brutally gunned down while trying to surrender. Rangers claimed he was killed in the heat of short, intense battle after his panicky horse rode into their ranks.

Whatever the actual facts, Northern troops were boiling for revenge. Custer was in the same frame, as well, for he had been plagued by Mosby’s constant harrassment long enough. Only the day before, his orderly had been captured while carrying a slaughtered sheep back to camp for Custer’s meal.

Six captive Rangers involved in the fight at Front Royal were captured and condemned to die. As a band slowly marched through Front Royal playing the dead march, the six prisoners were led to their deaths. Two Rangers, David Jones and Lucian Love, were shot in front of a church and left to die in their own blood. While that was occurring, Thomas Anderson was marched to an elm tree south of the town and shot.

A pair of horsemen next rode through Front Royal’s main streets, dragging 17-year-old civilian Henry Rhodes behind them with a rope. His crying mother tried to save the nearly unconscious boy, but her pleas were ignored. Rhodes was dragged to an open field north of town, where he was shot in the face by a volunteer who ’emptied his pistol upon him.’ His body, dumped in a wheel-barrow and covered with a sheet, was left at his mother’s door.

The last two prisoners, William Overby and a man called Carter, were led off to be hanged by a huge and wrathful crowd of soldiers. Overby stood ‘erect, defiant’ while Carter wept, listening to the band play ‘Love Not, the One You Love May Die.’ Just then Custer rode up, according to a town resident, ‘dressed in a splendid suit of silk velvet…. In his hand he had a large branch of damsons which he picked and ate as he rode along.’

Overby and Carter were taken to a large tree outside of town and offered freedom if they disclosed the location of Mosby’s headquarters. They both refused, and with hands tied behind their backs, the two prisoners were hanged. A sign was attached to Overby’s body reading, ‘Such is the Fate of All Mosby’s Gang.’

Custer and Mosby again clashed on October 7. Lieutenant John Meigs, a young topographical engineer of whom Sheridan was particularly fond, was returning to Custer’s headquarters with two orderlies in a heavy thunderstorm. They met three other riders who were wearing rubber ponchos over their uniforms, but since Meigs was behind Union lines he naively assumed that they were friendly. As Meigs approached, gunfire broke out, killing Meigs and one of the orderlies.

The second orderly got away and spread the news that Meigs had been coldly gunned down. Mosby’s men vehemently denied this (the facts seem to bear them out), but once again truth had no bearing on what would follow. A frustrated Sheridan wrote Grant that ‘Since I came into the Valley from Harper’s Ferry, every train, every small party, and every straggler has been bushwacked by people.’

Sheridan ordered Custer to destroy every house within a five-mile radius of where Meigs was killed. An artist in Sheridan’s camp, James Taylor, watched as Custer received his orders. ‘Never shall I forget the dramatic episode. Custer vaulting into the saddle, and exclaiming as he dashed away, ‘Look out for smoke!’ Custer rode off, declaring ‘I mean to return evil for evil until these scoundrels cease their depredations.’

‘In tears, Custer wept for his unfortunate orderly, who he said was,’shot down like a dog and stripped of all but his trousers’.’ In a short time, Taylor noticed ‘the ugly columns of smoke that rose in succession from the Valley like a funeral pall, told, too well, that he had fulfilled his orders to the letter.’

Mosby’s guerrillas continued to pester Sheridan’s forces in October. Correspondent Francis Long of the New York Herald ald wrote, ‘The intervening country between Harrisonburg and Winchester is literally swarming with guerrillas,’ Grant urged Sheridan to continue destroying whatever was useful for ‘if the war is to last another year, we want the Shenandoah Valley to remain a barren waste.’

For five days Custer tore into an 85-mile Shenandoah stretch, from Winchester to Waynesboro, burning barns and granaries, destroying bridges and ripping apart railroad track. Custer wanted ‘to put the fear of Hell in these people.’

Federal retaliation swiftly came on October 13, when Union colonel William Powell ordered the execution of Ranger A.C. ‘Ag’ Willis. A small tree was forced over double, and a noose was put over young Willis’s head. Then methodically attached to the tree, the tree was released. Willis’s body shot up into the sky; he was dead before he returned to earth. Near the end of October, Mosby received word of the earlier executions of his men and decided to retaliate in kind, hoping to ensure proper treatment for any of his men captured in the future. He informed Lee that Custer hanged six of his men and ‘It is my purpose to hang an equal number of Custer’s men whenever I capture them.’ Lee approved the action and so reported to Confederate Secretary of War James A. Seddon, who responded that he ‘cordially approved’ the orders. A brutal military policy was now receiving ‘cordial’ civilian approval.

Mosby told his men to sort through prisoners until they gathered 27 of Custer’s men. Facing the captives, Mosby mentioned, ‘There is but one man I would rather see than you and that is your commander.’ When some of the prisoners declared they had nothing to do with the Front Royal executions, Mosby replied, ‘I can’t identify the particular men that put the ropes around the necks of my Rangers, but I have a little account to settle with General Custer anyway.

‘Twenty-seven pieces of paper were placed into a hat. Seven of the pieces had numbers scrawled on them, the rest were blank. Those who drew a blank would be sent to Richmond or Libby prison, while a scrap of paper bearing a number meant death. Each prisoner was forced to reach into the hat and draw out his own fate. Any man unfortunate enough to pull out a number was walked over to the side under special guard. One Ranger grotesquely greeted them by saying, ‘We’ll give you a chance to stretch hemp.’

Some soldiers begged for their lives or stared into space. Others lay their heads on the nearest shoulder and cried. One man muttered prayers until it was his turn to draw. With trembling hand, he grabbed a piece from the hat, forced himself to gaze at it, then exclaimed in relief, ‘By God! I knew it would be so.’ Another man near him, who had drawn a number, quietly asked a friend to ‘Tell my mother I died like a man.’

Mosby learned that one of the condemed was a youthful drummer boy and ordered him spared. That meant a second death lottery for the 20 remaining prisoners to determine the last victim. Following a tortuous repeat drawing, the seventh doomed man was added to the group.

A detail of Rangers took the condemned men down the Winchester Turnpike to Berryville, as close to Custer’s camp as possible. In the confusion of the dark rainy night, prisoner George Soule of the 5th Michigan Cavalry managed to escape after punching a guard. Three of Custer’s men were hanged along the side of the turnpike, but it took so long that the Rangers became uneasy. In the words of Union Sergeant Charles Marvin, who also escaped, the Rangers decided ‘to shoot the balance of us, as ‘this hanging is too damned slow work.” The remaining three Union soldiers were systematically lined up near their lifeless cohorts, where a revolver was pointed at each from point blank range and fired. Happily for Marvin, the gun aimed at him misfired, and in the momentary confusion he knocked over his guard and disappeared into the woods. The other two, although grievously wounded also survived.

Before leaving, Mosby’s men attached a sign to one of the bodies reading, ‘These men have been hung in retaliation for an equal number of Colonel Mosby’s men hung by order of General Custer, at Front Royal. Measure for measure.’

Mosby dispatched Scout John Russell to deliver a letter to Sheridan. The letter explained the executions were in retaliation for Custer’s and Powell’s acts and in the future, ‘any prisoners falling into my hands will be treated with the kindness due to their condition, unless some new act of barbarity shall compel me, reluctantly, to adopt a line of policy repugnant to humanity.’ Sheridan issued orders to leave Mosby’s men alone if they did not harass Union troops, and further hangings were avoided.

Union devastation of the Shenandoah continued until Thanksgiving. Future combat shifted southward, out of the Valley, giving the battered Shenandoah time to replenish itself. But scars remained. A year later an English traveler compared the blackened Valley to a huge English moor. Years later a female resident, looking back at those days, wrote they were ‘indelibly photographed in my memory. I have often wished I could blot it out, for it clouded my childhood.’

For years, the fall of 1864 was known by Valley residents simply as ‘the Burning.’ The Civil War ultimately had departed the Valley, but it left behind permanent marks, physically on the land, and mentally on Shenandoah residents. As one Michigan trooper conceded, it was a ‘hard war.’

This article was written by John F. Wukovits and originally appeared in the March 2001 issue of America’s Civil War.

The author is incorrect in stating that Sheridan told his soldiers to leave Mosby’s men alone IF THEY DID NOT HARASS UNION TROOPS. That is plain nonsense. Mosby continued to “harass Union troops” with great success until he disbanded his command in April, 1865 after Appomattox.

Sheridan stopped any further such actions because he knew that Mosby caught far more of his men than he caught of Mosby’s and that the morale of his men – concerned about being captured anyway by Mosby – would suffer badly if they thought that their fate would be the rope or a bullet. Mosby was ready to fight under the black flag if that had been Sheridan’s desire but there can be no doubt that Mosby would have gotten the better of that battle and Sheridan knew it.

Interestingly enough, Sheridan sent a letter back to Mosby via Russell, the young scout Mosby had sent through the lines. Mosby’s letter to Sheridan is known among other reasons because he sent it to the newspapers so that his position was made as widely known as possible. However, Sheridan’s letter to Mosby has never been uncovered and published – at least to my knowledge. It is interesting to think what Sheridan said and why John Mosby never revealed it.

[…] 1864 he had been wounded twice but had quickly returned to duty. Mosby’s rangers were causing severe disruption to the Federal supply lines and Lt. Gen. Ulysses Grant ordered Maj. Gen. Philip Sheridan,”When any of Mosby’s men […]

[…] were the crops and barns filled with harvested crops, which were legitimate targets of war. Here is an article which sheds some light on the war in the Shenandoah Valley between the US Army and the guerrillas […]

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